HCID 136084607, compound → HCID 136186365, compound

HRID 413455Notes

Reaction equation

HRID 413455 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:33])[C:9]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[N:10][O:11][CH2:12][CH2:13][NH:14]C(OCC1C=CC=CC=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C(Cl)(Cl)Cl.[Pd]>[C:1]([O:5][C:6]([N:8]([CH3:33])[C:9]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[N:10][O:11][CH2:12][CH2:13][NH2:14])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 1

HCID 136084607HCID 136084607, compound

Product 1

HCID 136186365HCID 136186365, compoundYield 50.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of [N,N′-di(tert-butoxycarbonyl)] 2-(benzyloxycarbonylamino)ethoxy-N-methylguanidine (700 mg, 1.5 mmol), as prepared in the preceding step, 10% Pd/C (70 mg) in methanol (20 mL) and chloroform (5 mL) was hydrogenated under hydrogen (balloon) for 1 h. The catalyst was removed by filtration through Celite, the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (95:5 methylene chloride:methanol saturated with ammonia) to give the title compound as a colorless foam (250 mg, 50%). 1H-NMR (300 MHz, CDCl3) δ4.14 (t, J=5.0 Hz, 2H), 3.09 (s, 3H), 3.06 (q, J=5.0 Hz, 2H), 1.50 (s, 9H), 1.46 (s, 9H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography (95:5 methylene chloride:methanol saturated with ammonia)

Sources & evidence

ORD record
ord-1698a8463ffe4e57814984f985c31971
Source dataset
uspto-grants-2003_05
Patent number
US06566379B1

Reaction notes

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